Design, Synthesis, and Anti-HBV Activity of New Bis(l-amino acid) Ester Tenofovir Prodrugs

ACS Medicinal Chemistry Letters
2019.0

Abstract

A series of bis(l-amino acid) ester prodrugs of tenofovir (TFV) were designed and synthesized as new anti-HBV agents in this work. Four compounds <b>11, 12a, 12d</b>, and <b>13b</b> displayed better anti-HBV activity (IC<sub>50</sub>: 0.71-4.22 μM) than the parent drug TFV. The most active compound <b>11</b> (IC<sub>50</sub>: 0.71 μM), a bis(l-valine) ester prodrug of TFV, was found to have obviously greater AUC<sub>0-∞,</sub> <i>C</i> <sub>max</sub>, and F% than tenofovir disoproxil fumarate (TDF), and potent <i>in vivo</i> efficacy which is not inferior to TDF in a duck HBV (DHBV) model and a HBV DNA hydrodynamic mouse model, and it may serve as a promising lead compound for further anti-HBV drug discovery.

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